Piperidine → HCID 15024205, compound

HRID 1755599Notes

Reaction equation

HRID 1755599 reaction equation
[OH:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH3:17])([C:14]([OH:16])=O)[CH2:6][CH2:5]2.C1N=CN(C(N2C=NC=C2)=O)C=1.[NH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>C1COCC1>[OH:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([C:14]([N:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)=[O:16])([CH3:17])[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 8082PiperidineHCID 40634TroloxHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 15024205HCID 15024205, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

6-Hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (1.005 g, 4.00 mmol) in 22 mL THF was treated with 722.8 mg CDI (4.4 mmol) and stirred for 2 h at room temperature. The pale yellow solution was then treated with 450 μL (381 mg, 4.47 mmol) piperidine in 22 mL THF in 1-2 mL portions over 2 h. The reaction was stirred overnight at room temperature. The reaction was concentrated and the residue dissolved in 100 mL CH2Cl2 and sequentially washed with 50 mL 0.25 M HCl, 50 mL 1.0 M NaHCO3, 50 mL saturated NaCl and dried over Na2SO4. The organic phase was concentrated. Flash chromatography yielded 992 mg of (6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)(piperidin-1-yl)methanone as an off-white solid.

Workup

  1. stirringThe reaction was stirred overnight at room temperature
  2. concentrationThe reaction was concentrated
  3. dissolutionthe residue dissolved in 100 mL CH2Cl2
  4. washsequentially washed with 50 mL 0.25 M HCl, 50 mL 1.0 M NaHCO3, 50 mL saturated NaCl
  5. dry with materialdried over Na2SO4
  6. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-ef0193be38c947da9673ed896a1aeace
Source dataset
uspto-grants-2015_10
Patent number
US09169196B2

Reaction notes

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